Synthesis of Biaryls, Fluorenones, Cyclopenta[def]phenanthren-4-ones, and Benzophenones Based on Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-(Silyloxy)-2-en-1-ones

Abstract

Functionalized fluorenones were efficiently prepared in four steps. The [3+3] cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 3-(silyloxy)-2-en-1-ones afforded salicylates that were transformed into their enol triflates. The Suzuki cross-coupling reaction of the latter with arylboronic acids afforded 2-(methoxycarbonyl)biaryls that were subsequently transformed into the target molecules by intramolecular Friedel-Crafts acylation. In addition, 1-hydroxyfluorenones were prepared by cyclization of 3-aryl-3-(silyloxy­)-2-en-1-ones with 1,3-bis(silyloxy)buta-1,3-dienes and subsequent intramolecular Friedel-Crafts acylation of the 6-aryl­salicylates thus formed. In this context, the synthesis of novel cyclopenta[def]phenanthren-4-ones is reported. In addition, the synthesis of functionalized benzophenones is reported.

cyclizations - fluorenones - regioselectivity - silyl enol ethers

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CCDC 626089 and CCDC 698467 contain the crystallographic details of 7b and 7ab. These data are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: [phone], or [e-mail].